TW210287B - - Google Patents

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Publication number: TW210287B
Authority: TW; Taiwan
Prior art keywords: test; dihydro; keto; group; ethyl
Prior art date: 1991-03-01

Application number

TW081100863A

Other languages

English (en)

Chinese (zh)

Original Assignee

Kabushikaisha Ueno Seiyaku Oyo Kenkyujo

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-03-01

Filing date

1992-02-10

Publication date

1993-08-01

1992-02-10 Application filed by Kabushikaisha Ueno Seiyaku Oyo Kenkyujo filed Critical Kabushikaisha Ueno Seiyaku Oyo Kenkyujo

1993-08-01 Application granted granted Critical

1993-08-01 Publication of TW210287B publication Critical patent/TW210287B/zh

Links

206010030043 Ocular hypertension Diseases 0.000 claims abstract description 4
239000011885 synergistic combination Substances 0.000 claims abstract 2
-1 isopropyl ester Chemical class 0.000 claims description 50
150000001875 compounds Chemical class 0.000 claims description 43
239000000203 mixture Substances 0.000 claims description 21
230000004410 intraocular pressure Effects 0.000 claims description 18
239000003085 diluting agent Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000013589 supplement Substances 0.000 claims description 3
BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 claims description 2
229960000571 acetazolamide Drugs 0.000 claims description 2
150000002148 esters Chemical class 0.000 abstract description 11
238000000034 method Methods 0.000 abstract description 7
150000003839 salts Chemical class 0.000 abstract description 2
239000003489 carbonate dehydratase inhibitor Substances 0.000 abstract 1
239000002585 base Substances 0.000 description 49
125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
125000004429 atom Chemical group 0.000 description 20
125000000217 alkyl group Chemical group 0.000 description 19
238000002360 preparation method Methods 0.000 description 16
239000007789 gas Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
239000002253 acid Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
239000000126 substance Substances 0.000 description 11
150000001335 aliphatic alkanes Chemical class 0.000 description 9
201000010099 disease Diseases 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 8
239000000243 solution Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229920000954 Polyglycolide Polymers 0.000 description 7
239000012043 crude product Substances 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003814 drug Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000012298 atmosphere Substances 0.000 description 5
230000033228 biological regulation Effects 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
235000010409 propane-1,2-diol alginate Nutrition 0.000 description 5
150000003180 prostaglandins Chemical class 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
230000002195 synergetic effect Effects 0.000 description 5
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
238000006809 Jones oxidation reaction Methods 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical group 0.000 description 4
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000005907 alkyl ester group Chemical group 0.000 description 4
229940079593 drug Drugs 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
239000004095 hydrolyase inhibitor Substances 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
241000894007 species Species 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
229930194542 Keto Natural products 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
KKUKTXOBAWVSHC-UHFFFAOYSA-M dimethyl phosphate Chemical compound COP([O-])(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-M 0.000 description 3
229960002986 dinoprostone Drugs 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000007858 starting material Substances 0.000 description 3
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KZGNJLHBTZMSMD-UHFFFAOYSA-N C[Cu]C Chemical compound C[Cu]C KZGNJLHBTZMSMD-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
102100024423 Carbonic anhydrase 9 Human genes 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
229940123274 Dehydratase inhibitor Drugs 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
101710126089 Putative inactive carbonic anhydrase 5B-like protein Proteins 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002125 Sokalan® Polymers 0.000 description 2
206010041349 Somnolence Diseases 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000872 buffer Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
239000000832 lactitol Substances 0.000 description 2
VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 2
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229960003451 lactitol Drugs 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
229930182837 (R)-adrenaline Natural products 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
YRTJDWROBKPZNV-UHFFFAOYSA-N 15-Oxoprostaglandin E2 Natural products CCCCCC(=O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O YRTJDWROBKPZNV-UHFFFAOYSA-N 0.000 description 1
YRTJDWROBKPZNV-KMXMBPPJSA-N 15-dehydro-prostaglandin E2 Chemical compound CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O YRTJDWROBKPZNV-KMXMBPPJSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
XSDMOYYNBRDPOV-UHFFFAOYSA-N 5-butylnonan-5-yl(methyl)silane Chemical compound C(CCC)C([SiH2]C)(CCCC)CCCC XSDMOYYNBRDPOV-UHFFFAOYSA-N 0.000 description 1
108060003345 Adrenergic Receptor Proteins 0.000 description 1
102000017910 Adrenergic receptor Human genes 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
MTSFEGVZLSUPIB-UHFFFAOYSA-N C(CCCC)(=O)O.[Br] Chemical compound C(CCCC)(=O)O.[Br] MTSFEGVZLSUPIB-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 1
101150020741 Hpgds gene Proteins 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
241000283977 Oryctolagus Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
229960005164 acesulfame Drugs 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
MRSXAJAOWWFZJJ-UHFFFAOYSA-M acetazolamide sodium Chemical compound [Na+].CC(=O)NC1=NN=C(S([NH-])(=O)=O)S1 MRSXAJAOWWFZJJ-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
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150000002009 diols Chemical class 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000002309 gasification Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
KPSZWAJWFMFMFF-UHFFFAOYSA-N hept-5-enoic acid Chemical compound CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
125000000879 imine group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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230000003472 neutralizing effect Effects 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
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229940054534 ophthalmic solution Drugs 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
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239000012044 organic layer Substances 0.000 description 1
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238000010422 painting Methods 0.000 description 1
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230000000149 penetrating effect Effects 0.000 description 1
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235000019271 petrolatum Nutrition 0.000 description 1
125000006187 phenyl benzyl group Chemical group 0.000 description 1
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239000008363 phosphate buffer Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
LMPPOYVKJVJRTH-UHFFFAOYSA-N propan-2-yl hept-5-enoate Chemical compound C(C)(C)OC(CCCC=CC)=O LMPPOYVKJVJRTH-UHFFFAOYSA-N 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical group OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Ophthalmology & Optometry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

TW081100863A 1991-03-01 1992-02-10 TW210287B (lt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6132891		1991-03-01

Publications (1)

Publication Number	Publication Date
TW210287B true TW210287B (lt)	1993-08-01

Family

ID=13167964

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW081100863A TW210287B (lt)	1991-03-01	1992-02-10

Country Status (11)

Country	Link
US (1)	US5547968A (lt)
EP (1)	EP0501678B1 (lt)
JP (1)	JP2511611B2 (lt)
KR (1)	KR100221369B1 (lt)
AT (1)	ATE137407T1 (lt)
CA (1)	CA2061907C (lt)
DE (1)	DE69210286T2 (lt)
DK (1)	DK0501678T3 (lt)
ES (1)	ES2089387T3 (lt)
GR (1)	GR3019820T3 (lt)
TW (1)	TW210287B (lt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2270349A1 (en) *	1996-11-01	1998-05-14	Jesse A. May	Use of a combination of carbonic anhydrase inhibitors and prostaglandins for treating glaucoma
US6214381B1 (en)	1998-09-08	2001-04-10	Effcon, Inc.	Methazolamide composition and method of use
US7128903B2 (en) *	2001-10-03	2006-10-31	Innovative Pharmaceutical Concepts (Ipc) Inc.	Pharmaceutical preparations useful for treating tumors and lesions of the skin and the mucous membranes and methods and kits using same
AR043161A1 (es) *	2003-02-14	2005-07-20	Sucampo Pharmaceuticals Inc	Composicion oftalmica para tratar hipertension ocular y glaucoma
TWI348386B (en) *	2003-08-12	2011-09-11	R Tech Ueno Ltd	Composition and method for promoting hair growth
KR102074020B1 (ko) *	2012-07-13	2020-02-05	산텐 세이야꾸 가부시키가이샤	술폰아미드 화합물의 조합
US9980946B1 (en)	2017-01-25	2018-05-29	Effcon Laboratories, Inc.	Extended release methazolamide formulation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0242580B1 (en) *	1986-03-13	1993-04-28	The Trustees Of Columbia University In The City Of New York	Use of a, b and c prostaglandins and derivatives thereof to treat ocular hypertension and glaucoma
ATE76750T1 (de) *	1987-04-03	1992-06-15	Univ Columbia	Anwendung eines prostaglandins in mischung mit einem adrenergischen blocker zur verminderung des augen-innendruckes.
JPH0739343B2 (ja) *	1988-10-01	1995-05-01	株式会社アールテック・ウエノ	眼圧降下剤
GB2209939B (en) *	1987-09-18	1992-01-02	R Tech Ueno Ltd	The use of 13,14-dihydro-15-keto-prostaglandins as ocular hypotensive agents
EP0366279B1 (en) *	1988-10-01	1994-09-21	R-Tech Ueno Ltd.	Ocular hypotensive agents

1992
- 1992-02-10 TW TW081100863A patent/TW210287B/zh not_active IP Right Cessation
- 1992-02-20 EP EP92301412A patent/EP0501678B1/en not_active Expired - Lifetime
- 1992-02-20 DK DK92301412.0T patent/DK0501678T3/da active
- 1992-02-20 DE DE69210286T patent/DE69210286T2/de not_active Expired - Lifetime
- 1992-02-20 AT AT92301412T patent/ATE137407T1/de not_active IP Right Cessation
- 1992-02-20 ES ES92301412T patent/ES2089387T3/es not_active Expired - Lifetime
- 1992-02-26 CA CA002061907A patent/CA2061907C/en not_active Expired - Lifetime
- 1992-02-28 JP JP4043018A patent/JP2511611B2/ja not_active Expired - Lifetime
- 1992-02-29 KR KR1019920003307A patent/KR100221369B1/ko not_active Expired - Lifetime
1995
- 1995-06-07 US US08/487,637 patent/US5547968A/en not_active Expired - Lifetime
1996
- 1996-05-02 GR GR960401080T patent/GR3019820T3/el unknown

Also Published As

Publication number	Publication date
JPH0565227A (ja)	1993-03-19
KR920017654A (ko)	1992-10-21
EP0501678A2 (en)	1992-09-02
JP2511611B2 (ja)	1996-07-03
DK0501678T3 (da)	1996-05-28
ES2089387T3 (es)	1996-10-01
GR3019820T3 (en)	1996-08-31
KR100221369B1 (ko)	1999-09-15
EP0501678A3 (en)	1992-12-16
ATE137407T1 (de)	1996-05-15
DE69210286D1 (de)	1996-06-05
CA2061907C (en)	2003-04-08
EP0501678B1 (en)	1996-05-01
US5547968A (en)	1996-08-20
CA2061907A1 (en)	1992-09-02
DE69210286T2 (de)	1996-09-12

Legal Events

Date	Code	Title	Description
2012-03-21	MK4A	Expiration of patent term of an invention patent

Publication	Publication Date	Title
DE69511181T2 (de)	1999-12-02	Mittel für Behandlung der Leber-Gallenerkrankungen
EP0455264B1 (en)	1994-07-13	Ocular hypotensive agents
US5194429A (en)	1993-03-16	Ocular hypotensive agents
US5221763A (en)	1993-06-22	Prostaglandins of the F series
EP0289349A1 (en)	1988-11-02	Prostaglandins of the F series
US5426115A (en)	1995-06-20	Use of 15-keto-prostaglandin compound for improvement of encephalic function
EP0580268B1 (en)	1998-01-14	Ocular hypotensive agents
US5166178A (en)	1992-11-24	Ocular hypotensive agents
JP2597649B2 (ja)	1997-04-09	気管・気管支拡張剤
US6197821B1 (en)	2001-03-06	Endothelin antagonist
KR920007570B1 (ko)	1992-09-07	체온 상승제
US5397797A (en)	1995-03-14	Treatment of ocular hypertension with an ocular synergistic combination
KR960010435B1 (ko)	1996-08-01	상승병용을 이용한 안고혈압 치료
US5236907A (en)	1993-08-17	Ocular hypotensive agents
JP2511611B2 (ja)	1996-07-03	眼圧降下用医薬組成物
JP2511586B2 (ja)	1996-06-26	眼科用医薬組成物
EP0430551A2 (en)	1991-06-05	Treatment of cardiac dysfunction with 15-keto-prostaglandin compounds
EP0454429B1 (en)	1997-01-29	Use of 15-dehydroxy-16-oxoprostaglandin derivatives in the treatment of allergic diseases
DE3125271A1 (de)	1983-01-13	(delta)(pfeil hoch)8(pfeil hoch),(pfeil hoch)9(pfeil hoch)-prostaglandinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US6420422B1 (en)	2002-07-16	Ocular hypotensive agents
US20040225014A1 (en)	2004-11-11	Method for treating ocular hypertension and glaucoma
US5362751A (en)	1994-11-08	Tracheobronchodilator using 16-substituted PGEs
EP0469782A2 (en)	1992-02-05	Treatment of cataract with prostacyclin compounds
JPH0739343B2 (ja)	1995-05-01	眼圧降下剤
US5234954A (en)	1993-08-10	Treatment of hyperlipidemia with 15-keto-prostaglandin compounds